2-substituted pyrimidines

ABSTRACT

2-Substituted pyrimidines of the formula I 
                         
in which the index n and the substituents L, R a , R b , R c , R z , R u , R v , A′, A″ and A′″ are as defined in the description and:
     R 1  is C 3 -C 10 -alkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -alkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 10 -cycloalkenyl or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon and contains one to four heteroatoms from the group consisting of O, N and S,   R 2  is halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, C 3 -C 4 -alkenyloxy or C 3 -C 4 -alkynyloxy, where the alkyl, alkenyl and alkynyl radicals of R 2  may be substituted by halogen, cyano, nitro, C 1 -C 2 -alkoxy or C 1 -C 4 -alkoxycarbonyl, and   R 3  is cyano, CO 2 R a , C(═O)NR z R b , C(═O)—N—OR b , C(═S)—NR a R b , C(═NOR a )NR z R b , C(═NR a )NR z R b , C(═O)NR a —NR z R b , C(═N—NR z R c )NR a R b , C(═O)R a , C(═NOR b )R a , C(═N—NR z R b )R a , CR a R b —OR z , CR a R b —NR z R c , ON(═CR a R b ), O—C(═O)R a , NR a R b′ , NR a (C(═O)R b ), NR a (C(═O)OR b ), NR a (C(═O)—NR z R b ), NR a (C(═NR c )R b ), NR a (N═CR c R b ), NR a —NR z R b , NR z —OR a , NR a (C(═NR c )—NR z R b ), NR a (C(═NOR c )R b ),
 
processes for preparing these compounds, compositions comprising these compounds and their pesticidal use are described.

This application is a 371 of PCT/EP04/03335 filed Mar. 30, 2004.

The invention relates to 2-substituted pyrimidines of the formula I

in which the index and the substituents are as defined below:

-   -   n is an integer from 1 to 5, where at least one substituent L is        located in the ortho-position on the phenyl ring;    -   L is halogen, cyano, nitro, cyanato (OCN), C₁-C₈-alkyl,        C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy,        C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,        C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═S)—N(A′)A,        —C(═NA′)-SA, —C(═O)-A, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA),        N(A′)A, N(A′)-C(═O)-A, N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A,        S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A,        -   m is 0, 1 or 2;        -   A, A′, A″ independently of one another are hydrogen,            C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,            C₃-C₈-cycloalkenyl, phenyl, where the organic radicals may            be partially or fully halogenated or may be substituted by            cyano or C₁-C₄-alkoxy; or A and A′ together with the atoms            to which they are attached are a five- or six-membered            saturated, partially unsaturated or aromatic heterocycle            which contains one to four heteroatoms from the group            consisting of O, N and S;    -   R¹ is C₃-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₃-C₁₀-alkynyl,        C₃-C₁₂-cycloalkyl, C₃-C₁₀-cycloalkenyl or a five- to        ten-membered saturated, partially unsaturated or aromatic        heterocycle which is attached via carbon and contains one to        four heteroatoms from the group consisting of O, N and S,    -   R² is halogen, cyano, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₁-C₄-alkoxy, C₃-C₄-alkenyloxy or C₃-C₄-alkynyloxy, where the        alkyl, alkenyl and alkynyl radicals of R² may be substituted by        halogen, cyano, nitro, C₁-C₂-alkoxy or C₁-C₄-alkoxycarbonyl,

where the aliphatic, alicyclic or aromatic groups of the radicaldefinitions of L, R¹ and/or R² for their part may be partially or fullyhalogenated or may carry one to four groups R^(u):

-   -   R^(u) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl,        C₂-C₁₀-alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy,        C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,        C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═O)-A, —C(═O)—O-A,        —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A,        N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A, S(═O)_(m)—O-A or        S(═O)_(m)—N(A′)A, where m, A, A′, A″ are as defined above and        where the aliphatic, alicyclic or aromatic groups for their part        may be partially or fully halogenated or may carry one to three        groups R^(v), R^(v) having the same meaning as R^(u);    -   R³ is cyano, CO₂R^(a), C(═O)NR^(z)R^(b), C(═O)—N—OR^(b),        C(═S)—NR^(a)R^(b), C(═NOR^(a))NR^(z)R^(b),        C(═NR^(a))NR^(z)R^(b), C(═O)NR^(a)—NR^(z)R^(b),        C(═N—NR^(z)R^(c))NR^(a)R^(b), C(═O)R^(a), C(═NOR^(b))R^(a),        C(═N—NR^(z)R^(b))R^(a), CR^(a)R^(b)OR^(z),        CR^(a)R^(b)—NR^(z)R^(c), ON(═CR^(a)R^(b)), O—C(═O)R^(a),        NR^(a)R^(b′), NR^(a)(C(═O)R^(b)), NR^(a)(C(═O)OR^(b)),        NR^(a)(C(═O)—NR^(z)R^(b)), NR^(a)(C(═NR^(c))R^(b)),        NR^(a)(N═CR^(c)R^(b)), NR^(a)—NR^(z)R^(b), NR^(z)—OR^(a),        NR^(a)(C(═NR^(c))—NR^(z)R^(b)), NR^(a)(C(═NOR^(c))R^(b)); where        -   R^(a),R^(b),R^(c) independently of one another are hydrogen,            C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl            or C₄-C₆-cycloalkenyl;        -   R^(b′) has the same meanings as R^(b), except for hydrogen;        -   R^(z) has the same meanings as R^(a) and may additionally be            —CO—R^(a);

where the aliphatic or alicyclic groups of the radical definitions ofR^(a),R^(b),R^(c) or R^(z) for their part may be partially or fullyhalogenated or may carry one to four groups R^(w):

-   -   R^(w) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl,        C₂-C₁₀-alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy,        C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,        C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, and where two of the        radicals R^(a), R^(b), R^(c) or R^(z) together with the atoms to        which they are attached may form a five- or six-membered        saturated, partially unsaturated or aromatic heterocycle which        contains one to four heteroatoms from the group consisting of O,        N and S.

Moreover, the invention relates to a process for preparing thesecompounds, to compositions comprising them and to their use forcontrolling phytopathogenic harmful fungi.

Fungicidal pyrimidines carrying a cyanamino substituent in the2-position are known from WO-A 01/96314.

However, in many cases their activity is unsatisfactory. It was anobject of the present invention to provide compounds having improvedactivity.

We have found that this object is achieved by the pyrimidines of theformula I defined at the outset. Moreover, we have found processes fortheir preparation and compositions comprising them for controllingharmful fungi.

The compounds I can be obtained by different routes.

1) It is possible, for example, to use dichloropyrimidines of theformula V, whose preparation is described in detail in WO-A 02/074753,as starting materials. Generally, initially the substituent R¹ isintroduced in the 4-position on the pyrimidine ring by coupling withorganometallic reagents (see Scheme 1), giving the compounds of theformula VI.

In one embodiment of this process, the reaction is carried out withtransition metal catalysis, such as Ni or Pd catalysis. The radical R²can be introduced analogously into the 6-position on the pyrimidinering. In some cases it may be advisable to change the order and tointroduce the substituent R² first.

In the formulae (R¹)_(y-w)X_(w)-M^(y) and (R²)_(y-w)X_(w)-M^(y), M is ametal ion of valency Y, such as, for example, B, Zn, Mg, Cu or Sn, X ischlorine, bromine, iodine or hydroxyl, R¹ is preferably C₃-C₈-alkyl orC₃-C₈-alkenyl and R² is in particular C₁-C₄-alkyl and w is a number from0 to 3. This reaction can be carried out, for example, analogously tothe following methods: J. Chem. Soc. Perkin Trans. 1, 1187 (1994), ibid1, 2345 (1996); WO-A 99/41255; Aust. J. Chem. 43 (1990), 733; J. Org.Chem. 43 (1978), 358; J. Chem. Soc. Chem. Commun. 866 (1979);Tetrahedron Lett. 34 (1993), 8267; ibid 33 (1992), 413.

What was said above applies in particular to the preparation ofcompounds in which R² is an alkyl group. If R² is a cyano group or analkoxy substituent, the radical R² can be introduced by reaction withalkali metal cyanides and alkali metal alkoxides, respectively.

Sulfones of the formula IIIb are obtained by oxidizing the correspondingthio compounds IIIa. They are prepared under the conditions known fromWO 02/88127.

Suitable oxidizing agents have been found to be in particular hydrogenperoxide or peracids of organic carboxylic acids. However, the oxidationcan also be carried out using, for example, selenium dioxide.

2) Scheme 2 shows a similar synthesis route as Scheme 1 in which only afew synthesis sequences were exchanged. The route shown in Scheme 1 isof interest in particular for preparing the compounds I′ in which R² ischlorine, and for compounds I in which R² is a cyano or alkoxy group.

The reaction route shown in Scheme 1 allows the introduction of radicalsR³ attached via carbon, such as cyano, or radicals attached vianitrogen, such as hydroxylamine, amidine or guanidine, in the 2-positionon the pyrimidine ring. Starting from the cyano radical, it is in turnpossible to construct other carbon-bound radicals in the 2-positionusing methods known from the literature: for example the carboxylateradical CO₂R^(a) by hydrolysis or the acyl radical C(═O)R^(a) byGrignard reaction.

A further advantageous route for preparing the compounds I is shown inScheme 3. Here, the substituent R^(2′) is a radical which is attachedvia carbon, such as alkyl, but not cyano. As already discussed in moredetail for the synthesis route shown in Scheme 1, it is possible tosynthesize, in the manner mentioned above, various radicals attached viacarbon, starting from the cyano radical which is introduced directly.

3) The pyrimidine ring is synthesized using the routes described in WO97/49697, DD 151404 and JOC 17 (1952), 1320.

The bromination is preferably carried out using elemental bromine orN-bromosuccinimide. This step can advantageously be carried out in aninert solvent, such as chlorobenzene, nitrobenzene, methylene chloride,chloroform, carbon tetrachloride or a carboxylic acid such as aceticacid.

Suitable chlorinating agents [Cl] for converting the hydroxyl compoundsIX to the compounds X are, for example, POCl₃, PCl₃/Cl₂ or PCl₅, ormixtures of these reagents. The reaction can be carried out in excesschlorinating agent (POCl₃) or in an inert solvent, such as, for example,acetonitrile, toluene, chlorobenzene or 1,2-dichloroethane. Preferenceis given to carrying out the reaction in POCl₃. The chlorinated productcan be prepared analogously to the method described in WO 02/74753 onpage 4, line 25.

This reaction is usually carried out between 10 and 180° C. Forpractical reasons, the reaction temperature usually corresponds to theboiling point of the chlorinating agent used (POCl₃) or to the boilingpoint of the solvent. The process is advantageously carried out withaddition of N,N-dimethylformamide in catalytic or substoichiometricamounts or of nitrogen bases, such as, for example, N,N-dimethylaniline.

In the case of reagents which are sufficiently nucleophilic, R³ and thepyrimidine ring are attached under the conditions of nucleophilicsubstitution; usually at from 0 to 200° C., preferably at from 10 to150° C., in the presence of a dipolar aprotic solvent, such asN,N-dimethylformamide, tetrahydrofuran or acetonitrile [cf. DE-A 39 01084; Chimia 50 (1996), 525-530; Khim. Geterotsikl. Soedin 12 (1998),1696-1697].

In general, the components are employed in an approximatelystoichiometric ratio. However, it may be advantageous to use an excessof the nucleophile of the formula R³—H.

In general, the reaction is carried out in the presence of a base whichcan be used in equimolar amounts or else in excess. Suitable bases arealkali metal carbonates and bicarbonates, for example Na₂CO₃ and NaHCO₃,nitrogen bases, such as triethylamine, tributylamine and pyridine,alkali metal alkoxides, such as sodium methoxide or potassiumtert-butoxide, alkali metal amides, such as NaNH₂, or else alkali metalhydrides, such as LiH or NaH.

Moreover, the pyridine and the phenyl ring can also be linked under thereaction conditions of the Suzuki coupling (JOC 67 (2002), 3643; Angew.Chem. 114 (2002), 4350, and literature cited therein).

4) When constructing the pyrimidine ring, it may be advantageous tointroduce the substituent R³ together with the amidine component, asshown in Scheme 4a. In this, R^(2′) is again a radical attached viacarbon, such as alkyl (but not cyano).

If, in the reaction shown in Scheme 4a, the specific amidine componentreacted with the 1,3-dicarbonyl compound XIIa is guanidine,2-aminopyrimidines are obtained. Using alkylating and acylating methodsknown from the literature, it is thus possible to synthesize in a simplemanner pyrimidines according to the invention having a radical attachedvia nitrogen in the 2-position. In these cases, R² is preferably aradical attached via carbon (except for cyano). For compounds havingthis substitution pattern, this is an interesting alternative to methods1 to 3 mentioned above.

Conversely, pyrimidines I in which R² is halogen or an alkoxy group canbe prepared advantageously using the route shown in Scheme 4b. Usingketoesters XIIb and amidines as starting materials, compounds XIII areobtained which, depending on the nature of the substituent R², can beconverted into the respective target compounds I or I′.

5) As already mentioned repeatedly above, for preparing the pyrimidinesI in which R³ is a radical attached via carbon, such as alkyl (but notcyano), it is advantageous to use, as starting materials, 1,3-dicarbonylcompounds (XIIa). Reaction with urea gives—as shown in Scheme 5—thecompounds XIV, which can be chlorinated to give XV.

In the case of strong nucleophiles, the substituent R³ (last processstep) is introduced under the conditions of nucleophilic substitution.

Moreover, the bond can also be formed with transition metal catalysis,such as, for example, under the reaction conditions of the Suzukicoupling.

6) Scheme 6 additionally shows how the chain of the substituent R¹ canbe extended.

The synthesis route shown in Scheme 7 is similar to those shown inSchemes 2 and 6. Here, initially the chain is extended to construct thelipophilic radical in the 6-position on the pyrimidine ring. The radicalR³ is only introduced at the end. This variant is recommended forsubstituents R³ sensitive to hydrolysis.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separating the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of colorless orslightly brownish viscous oils which are purified or freed from volatilecomponents under reduced pressure and at moderately elevatedtemperature. If the intermediates and end products are obtained assolids, purification can also be carried out by recrystallization ordigestion.

If individual compounds I cannot be obtained by the routes describedabove, they can be prepared by derivatization of other compounds I.

If the synthesis yields mixtures of isomers, a separation is generallynot necessarily required since in some cases the individual isomers canbe converted into one another during work-up for use or duringapplication (for example under the action of light, acids or bases).Such conversions may also take place after use, for example in thetreatment of plants in the treated plants or in the harmful fungus to becontrolled.

In the definitions of the symbols given in the formulae above,collective terms were used which are generally representative of thefollowing substituents:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: saturated straight-chain or branched hydrocarbon radicals having1 to 4, 6, 8 or 10 carbon atoms, for example C₁-C₆-alkyl such as methyl,ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethyipropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

haloalkyl: straight-chain or branched alkyl groups having 1 to 10 carbonatoms (as mentioned above), where in these groups some or all of thehydrogen atoms may be replaced by halogen atoms as mentioned above, forexample C₁-C₂-haloalkyl, such as chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or1,1,1-trifluoroprop-2-yl;

alkenyl: unsaturated straight-chain or branched hydrocarbon radicalshaving 2 to 4, 6, 8 or 10 carbon atoms and a double bond in anyposition, for example C₂-C₆-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

alkadienyl: unsaturated straight-chain or branched hydrocarbon radicalshaving 4, 6, 8 or 10 carbon atoms and two double bonds in any position;

haloalkenyl: unsaturated straight-chain or branched hydrocarbon radicalshaving 2 to 10 carbon atoms and a double bond in any position (asmentioned above), where in these groups some or all of the hydrogenatoms may be replaced by halogen atoms as mentioned above, in particularby fluorine, chlorine and bromine;

alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6,8 or 10 carbon atoms and a triple bond in any position, for exampleC₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and1-ethyl-1-methyl-2-propynyl;

cycloalkyl: mono- or bicyclic saturated hydrocarbon groups having 3 to 6or 8 carbon ring members, for example C₃-C₈-cycloalkyl such ascyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl;

five- or six-membered saturated, partially unsaturated or aromaticheterocycle which contains one to four heteroatoms from the groupconsisting of O, N and S:

-   -   5- or 6-membered heterocyclyl which contains one to three        nitrogen atoms and/or one oxygen or sulfur atom or one or two        oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl,        3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,        2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl,        4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl,        4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,        4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,        4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,        4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl,        4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl,        1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl,        1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,        1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,        1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,        2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,        2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,        2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl,        2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,        2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,        2-isoxazolin4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,        2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,        2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,        2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,        2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,        2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,        2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,        2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,        3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol4-yl,        3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,        4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol4-yl,        4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl,        2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,        2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,        3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol4-yl,        3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,        3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol4-yl, 2-piperidinyl,        3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,        2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,        3-hexahydropyridazinyl, 4-hexahydropyridazinyl,        2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl,        5-hexahydropyrimidinyl, 2-piperazinyl,        1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl and        morpholinyl;    -   5-membered heteroaryl which contains one to four nitrogen atoms        or one to three nitrogen atoms and one sulfur or oxygen atom:        5-membered heteroaryl groups which, in addition to carbon atoms,        may contain one to four nitrogen atoms or one to three nitrogen        atoms and one sulfur or oxygen atom as ring members, for example        2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,        3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,        4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl,        5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,        4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,        1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,        1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,        1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl        and 1,3,4-triazol-2-yl;    -   6-membered heteroaryl which contains one to three or one to four        nitrogen atoms: 6-membered heteroaryl groups which, in addition        to carbon atoms, may contain one to three and one to four        nitrogen atoms, respectively, as ring members, for example        2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl,        4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl,        2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

The scope of the present invention includes the (R) and (S) isomers andthe racemates of compounds of the formula I having chiral centers.

Hereinbelow, the embodiments of the invention are described in moredetail.

Pyrimidines I where the index and the substituents are as defined below:

-   -   n is an integer from 1 to 5, where at least one substituent L is        located in the ortho-position on the phenyl ring        -   L is halogen, cyano, nitro, cyanato (OCN), C₁-C₈-alkyl,            C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₆-alkoxy,            C₂-C₁₀-alkenyloxy, C₁-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,            C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy,            C₃-C₆-cycloalkenyloxy, —C(═S)—N(A′)A, —C(═NA′)-SA, —C(═O)-A,            —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A,            N(A′)-C(═O)-A, N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A,            S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A,            -   m is 0, 1 or 2;            -   A, A′, A″ independently of one another are hydrogen,                C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,                C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, phenyl, where the                organic radicals may be partially or fully halogenated                or may be substituted by cyano or C₁-C₄-alkoxy; or A and                A′ together with the atoms to which they are attached                are a five- or six-membered saturated, partially                unsaturated or aromatic heterocycle which contains one                to four heteroatoms from the group consisting of O, N                and S;        -   R¹ is C₃-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₃-C₁₀-alkynyl,            C₃-C₁₂-cycloalkyl, C₃-C₁₀-cycloalkenyl or a five- to            ten-membered saturated, partially unsaturated or aromatic            heterocycle which is attached via carbon and contains one to            four heteroatoms from the group consisting of O, N and S,        -   R² is halogen, cyano, C₁-C₄-alkyl, C₂-C₄-alkenyl,            C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy or            C₃-C₄-alkynyloxy, where the alkyl, alkenyl and alkynyl            radicals of R² may be substituted by halogen, cyano, nitro,            C₁-C₂-alkoxy or C₁-C₄-alkoxycarbonyl        -   where the aliphatic, alicyclic or aromatic groups of the            radical definitions of L, R¹ and/or R² for their part may be            partially or fully halogenated or may carry one to four            groups R^(u):            -   R^(u) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl,                C₂-C₁₀-alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy,                C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,                C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═O)-A,                —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A,                N(A′)-C(═O)-A, N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A,                S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A, where m, A, A′, A″                are as defined above and where the aliphatic, alicyclic                or aromatic groups for their part may be partially or                fully halogenated or may carry one to three groups                R^(v), R^(v) having the same meaning as R^(u);        -   R³ is cyano, CO₂R^(a), C(═O)NR^(z)R^(b), C(═S)NR^(z)R^(b),            C(═NOR^(a))NR^(z)R^(b), C(═NR^(a))NR^(z)R^(b),            C(═O)NR^(a)—NR^(z)R^(b), C(═N—NR^(z)R^(c))NR^(a)R^(b),            C(═O)R^(a), C(═NOR^(b))R^(a), C(═N—NR^(z)R^(b))R^(a),            CR^(a)R^(b)—OR^(z), CR^(a)R^(b)—R^(z)R^(c),            ON(═CR^(a)R^(b)), O—C(═O)R^(a), NR^(a)R^(b′),            NR^(a)(C(═O)R^(b)), NR^(a)(C(═O)OR^(b)),            NR^(a)(C(═O)—NR^(z)R^(b)), N—R^(a)(C(═NR^(c))R^(b)),            NR^(a)(N═CR^(c)R^(b)), NR^(a)—NR^(z)R^(b), NR^(a)—OR^(z),            NR^(a)(C(═NR^(c))—NR^(z)R^(b)), NR^(a)(C(═NOR^(c))R^(b));            where            -   R^(a),R^(b),R^(c) independently of one another are                hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,                C₃-C₆-cycloalkyl or C₄-C₆-cycloalkenyl;            -   R^(b′) has the same meanings as R^(b), except for                hydrogen;            -   R^(z) has the same meanings as R^(a) and may                additionally be —CO—R^(a);        -   where the aliphatic or alicyclic groups of the radical            definitions of R^(a),R^(b),R^(c) or R^(z) for their part may            be partially or fully halogenated or may carry one to four            groups R^(w):            -   R^(w) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl,                C₂-C₁₀-alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy,                C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,                C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, and where two                of the radicals R^(a), R^(b), R^(c) or R^(z) together                with the atoms to which they are attached may form a                five- or six-membered saturated, partially unsaturated                or aromatic heterocycle which contains one to four                heteroatoms from the group consisting of O, N and S.

With a view to the intended use of the pyrimidines of the formula 1,particular preference is given to the following meanings of thesubstituents, in each case on their own or in combination:

Preference is given to compounds I in which R¹ is C₃-C₈-alkyl,C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl.

Particular preference is given to compounds I in which R¹ is C₃-C₆-alkylor C₃-C₆-haloalkyl.

In addition, preference is given to compounds I in which R¹ isC₃-C₈-alkenyl or C₃-C₈-alkynyl.

Moreover, preference is given to compounds I in which R¹ isC₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl, which radicals may besubstituted by C₁-C₄-alkyl or halogen.

Particular preference is given to compounds I in which R^(u) is halogen,cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₆-alkoxy,C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,C₅-C₆-cycloalkenyl, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), where thealiphatic or alicyclic groups for their part may be partially or fullyhalogenated or may carry one to three groups R^(v), R^(v) having thesame meaning as R^(u).

Particular preference is given to compounds I in which R^(u) is halogen,cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyl,C₅-C₆-cycloalkenyl.

Particular preference is also given to compounds I in which R² isC₁-C₄-alkyl which may be substituted by halogen.

Moreover, particular preference is given to compounds I in which R² ishalogen, cyano, C₁-C₄-alkyl or C₁-C₄-alkoxy.

Especially preferred are compounds I in which R² is methyl, ethyl,cyano, methoxy or chlorine.

Preference is furthermore given to pyrimidines of the formula I in whichR³ is cyano, CO₂R^(a), C(═O)NR^(z)R^(b), C(═NOR^(a))NR^(z)R^(b),C(═NR^(a))NR^(z)R^(b), C(═O)NR^(a)—NR^(z)R^(b),C(═N—NR^(z)R^(c))NR^(a)R^(b), C(═O)R^(a), C(═NOR^(b))R^(a),C(═O)—N(R^(a))—OR^(b), C(═S)—NR^(a)R^(b), C(═N—NR^(z)R^(b))R^(a),CR^(a)R^(b)—OR^(z) or CR^(a)R^(b)—NR^(z)R^(c).

Particular preference is given to pyrimidines of the formula I in whichR³ is cyano, C(═O)NR^(z)R^(b), C(═O)—N(R^(a))—OR^(b), C(═S)—NR^(a)R^(b),C(═NOR^(a))NR^(z)R^(b), C(═NOR^(b))R^(a), C(═N—NR^(z)R^(b))R^(a) orCR^(a)R^(b)—NR^(z)R^(c).

Moreover, preference is given to pyrimidines of the formula I in whichR³ is ON(═CR^(a)R^(b)) or O—C(═O)R^(a).

Furthermore, preference is given to pyrimidines of the formula I inwhich R³ is NR^(a)R^(b), NR^(a)(C(═O)R^(b)), NR^(a)(C(═O)OR^(b)),NR^(a)(C(═O)—NR^(z)R^(b)), NR^(a)(C(═NR^(a))R^(b)),NR^(a)(N═CR^(c)R^(b)), NR^(a)—NR^(z)R^(b), NR^(z)—OR^(a),NR^(a)(C(═NR^(c))—NR^(z)R^(b)), NR^(a)(C(═NOR^(c))R^(b)).

Especially preferred are pyrimidines of the formula I in which R³ isNR^(a)(C(═O)R^(b)), NR^(a)(C(═O)OR^(b)), NR^(a)(N═CR^(c)R^(b)),NR^(z)—OR^(a).

R^(a), R^(b) and R^(c) are preferably independently of one anotherhydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₃-C₆-cycloalkyl.

R^(z) preferably has the preferred meanings of R^(a), R^(b) and R^(c)mentioned above. Particular preference is given to the additionalmeaning —CO—R^(a).

Moreover, preference is given to pyrimidines I where the phenyl groupsubstituted by L_(n) is the group B

where # is the point of attachment to the pyrimidine skeleton

-   -   L¹ is fluorine, chlorine, CH₃ or CF₃;    -   L²,L⁴ independently of one another are hydrogen, CH₃ or        fluorine;    -   L³ is hydrogen, fluorine, chlorine, bromine, cyano, nitro, CH₃,        SCH₃, OCH₃, SO₂CH₃, CO—NH₂, CO—NHCH₃, CO—NHC₂H₅, CO—N(CH₃)₂,        NH—C(═O)CH₃, N(CH₃)—C(═O)CH₃ or COOCH₃ and    -   L⁵ is hydrogen, fluorine, chlorine or CH₃.

Moreover, particular preference is given to pyrimidines I where theindex n and the substituents L¹ to L⁵ are as defined below:

-   -   n 1 to 3;    -   L is halogen, cyano, nitro, C₁-C₈-alkyl, C₂-C₁₀-alkenyl,        C₂-C₁₀-alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy,        C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,        C₃-C₆-cycloalkoxy, —C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA),        N(A′)A, N(A′)-C(═O)-A or S(═O)_(m)-A;        -   m is 0, 1 or 2;        -   A, A′, A″ independently of one another are hydrogen,            C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, where the organic            radicals may be partially or fully halogenated or may be            substituted by cyano or C₁-C₄-alkoxy, or A and A′ together            with the atoms to which they are attached are a five- or            six-membered saturated heterocycle which contains one to            four heteroatoms from the group consisting of O, N and S.

Especially preferred are pyrimidines I where the substituents L¹ to L⁵are as defined below:

-   -   L is halogen, cyano, C₁-C₈-alkyl, C₁-C₆-alkoxy, —C(═O)—O-A,        —C(═O)—N(A′)A,        -   A, A′, A″ independently of one another are hydrogen,            C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl.

In particular with a view to their use, preference is given to thecompounds I compiled in the tables below. Moreover, the groups mentionedfor a substituent in the tables are per se, independently of thecombination in which they are mentioned, a particularly preferredembodiment of the substituent in question.

-   Table 1

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-chloro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 2

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 3

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dichloro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 4

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-methyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 5

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trifluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 6

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-fluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 7

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxycarbonyl, R² is methyl andR¹ corresponds for each compound to one row of Table A

-   Table 8

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-CN, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 9

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,5-trifluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 10

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dichloro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 11

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro, R² is methyl and R¹ correspondsfor each compound to one row of Table A

-   Table 12

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro, R² is methyl and R¹ correspondsfor each compound to one row of Table A

-   Table 13

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-difluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 14

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-chloro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 15

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-fluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 16

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3-difluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 17

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-difluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 18

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3,4-trifluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 19

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl, R² is methyl and R¹ correspondsfor each compound to one row of Table A

-   Table 20

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dimethyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 21

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-chloro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 22

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 23

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dimethyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 24

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trimethyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 25

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-cyano, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 26

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 27

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxycarbonyl, R² is methyland R¹ corresponds for each compound to one row of Table A

-   Table 28

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxy, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 29

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 30

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxycarbonyl, R² is methyl andR¹ corresponds for each compound to one row of Table A

-   Table 31

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-bromo, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 32

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-cyano, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 33

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxy, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 34

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,3-methyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 35

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 36

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-cyano, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 37

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-bromo, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 38

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,5-fluoro, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 39

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxy, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 40

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxycarbonyl, R² is methyl andR¹ corresponds for each compound to one row of Table A

-   Table 41

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl,4-brom, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 42

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-bromo, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 43

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxy, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 44

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,5-methyl, R² is methyl and R¹corresponds for each compound to one row of Table A

-   Table 45

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is pentafluoro, R² is methyl and R¹ correspondsfor each compound to one row of Table A

-   Table 46

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-chloro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 47

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 48

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dichloro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 49

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-methyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 50

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trifluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 51

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-fluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 52

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxycarbonyl, R² is chloro andR¹ corresponds for each compound to one row of Table A

-   Table 53

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-CN, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 54

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,5-trifluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 55

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dichloro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 56

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro, R² is chloro and R¹ correspondsfor each compound to one row of Table A

-   Table 57

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro, R² is chloro and R¹ correspondsfor each compound to one row of Table A

-   Table 58

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-difluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 59

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-chloro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 60

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-fluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 61

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3-difluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 62

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-difluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 63

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3,4-trifluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 64

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl, R² is chloro and R¹ correspondsfor each compound to one row of Table A

-   Table 65

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dimethyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 66

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-chloro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 67

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 68

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dimethyl, R2 is chloro and R¹corresponds for each compound to one row of Table A

-   Table 69

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trimethyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 70

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-cyano, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 71

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 72

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxycarbonyl, R² is chloroand R¹ corresponds for each compound to one row of Table A

-   Table 73

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxy, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 74

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 75

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxycarbonyl, R² is chloro andR¹ corresponds for each compound to one row of Table A

-   Table 76

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-bromo, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 77

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-cyano, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 78

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxy, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 79

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,3-methyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 80

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 81

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-cyano, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 82

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-bromo, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 83

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,5-fluoro, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 84

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxy, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 85

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxycarbonyl, R² is chloro andR¹ corresponds for each compound to one row of Table A

-   Table 86

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl,4-bromo, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 87

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-bromo, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 88

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxy, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 89

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,5-methyl, R² is chloro and R¹corresponds for each compound to one row of Table A

-   Table 90

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is pentafluoro, R² is chloro and R¹ correspondsfor each compound to one row of Table A

-   Table 91

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-chloro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 92

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 93

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dichloro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 94

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-methyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 95

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trifluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 96

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-fluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 97

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxycarbonyl, R² is methoxyand R¹ corresponds for each compound to one row of Table A

-   Table 98

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-CN, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 99

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,5-trifluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 100

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dichloro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 101

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro, R² is methoxy and R¹ correspondsfor each compound to one row of Table A

-   Table 102

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro, R² is methoxy and R¹ correspondsfor each compound to one row of Table A

-   Table 103

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-difluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 104

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-chloro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 105

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-fluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 106

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3-difluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 107

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-difluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 108

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3,4-trifluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 109

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl, R² is methoxy and R¹ correspondsfor each compound to one row of Table A

-   Table 110

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dimethyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 111

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-chloro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 112

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 113

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dimethyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 114

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trimethyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 115

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-cyano, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 116

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 117

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxycarbonyl, R² ismethoxy and R¹ corresponds for each compound to one row of Table A

-   Table 118

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxy, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 119

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 120

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxycarbonyl, R² is methoxyand R¹ corresponds for each compound to one row of Table A

-   Table 121

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-bromo, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 122

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-cyano, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 123

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxy, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 124

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,3-methyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 125

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 126

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-cyano, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 127

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-bromo, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 128

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,5-fluoro, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 129

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxy, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 130

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxycarbonyl, R² is methoxyand R¹ corresponds for each compound to one row of Table A

-   Table 131

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl,4-bromo, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 132

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-bromo, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 133

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxy, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 134

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,5-methyl, R² is methoxy and R¹corresponds for each compound to one row of Table A

-   Table 135

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is pentafluoro, R² methoxy and R¹ correspondsfor each compound to one row of Table A

-   Table 136

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-chloro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 137

Compounds of the formula IA, IB, IC, ID, IE,.IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 138

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dichloro, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 139

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,6-methyl, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 140

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trifluoro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 141

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-fluoro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 142

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxycarbonyl, R² is cyano andR¹ corresponds for each compound to one row of Table A

-   Table 143

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-CN, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 144

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,5-trifluoro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 145

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dichloro, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 146

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro, R² is cyano and R¹ corresponds foreach compound to one row of Table A

-   Table 147

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro, R² is cyano and R¹ corresponds foreach compound to one row of Table A

-   Table 148

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-difluoro, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 149

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-chloro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 150

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-fluoro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 151

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3-difluoro, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 152

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-difluoro, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 153

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,3,4-trifluoro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 154

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl, R² is cyano and R¹ corresponds foreach compound to one row of Table A

-   Table 155

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4-dimethyl, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 156

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-chloro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 157

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL,IM,IN and IO in which L_(n) is 2-fluoro,4-methyl, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 158

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-dimethyl, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 159

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,4,6-trimethyl, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 160

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-cyano, R²is cyano and R¹corresponds for each compound to one row of Table A

-   Table 161

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methyl, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 162

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxycarbonyl, R² is cyanoand R¹ corresponds for each compound to one row of Table A

-   Table 163

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxy, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 164

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methyl, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 165

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-methoxycarbonyl, R² is cyano andR¹ corresponds for each compound to one row of Table A

-   Table 166

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-bromo, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 167

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-chloro,4-cyano, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 168

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,6-difluoro,4-methoxy, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 169

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,3-methyl, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 170

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl, R² is cyano and R¹ correspondsfor each compound to one row of Table A

-   Table 171

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-cyano, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 172

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-bromo, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 173

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,5-fluoro, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 174

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxy, R²is cyano and R¹corresponds for each compound to one row of Table A

-   Table 175

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-methyl,4-methoxycarbonyl, R² is cyano andR¹ corresponds for each compound to one row of Table A

-   Table 176

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2,5-dimethyl,4-bromo, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 177

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-bromo, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 178

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,4-methoxy, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 179

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is 2-fluoro,5-methyl, R² is cyano and R¹corresponds for each compound to one row of Table A

-   Table 180

Compounds of the formula IA, IB, IC, ID, IE, IF, IG, IH, II, IK, IL, IM,IN and IO in which L_(n) is pentafluoro, R² is cyano and R¹ correspondsfor each compound to one row of Table A

TABLE A No. R¹ A-1 CH₃ A-2 CH₂CH₃ A-3 CH₂CH₂CH₃ A-4 CH(CH₃)₂ A-5CH₂CH(CH₃)₂ A-6 (±)CH(CH₃)CH₂CH₃ A-7 (R)CH(CH₃)CH₂CH₃ A-8(S)CH(CH₃)CH₂CH₃ A-9 (CH₂)₃CH₃ A-10 C(CH₃)₃ A-11 (CH₂)₄CH₃ A-12CH(CH₂CH₃)₂ A-13 CH₂CH₂CH(CH₃)₂ A-14 (±)CH(CH₃)(CH₂)₂CH₃ A-15(R)CH(CH₃)(CH₂)₂CH₃ A-16 (S)CH(CH₃)(CH₂)₂CH₃ A-17 (±)CH₂CH(CH₃)CH₂CH₃A-18 (R)CH₂CH(CH₃)CH₂CH₃ A-19 (S)CH₂CH(CH₃)CH₂CH₃ A-20(±)CH(CH₃)CH(CH₃)₂ A-21 (R)CH(CH₃)CH(CH₃)₂ A-22 (S)CH(CH₃)CH(CH₃)₂ A-23(CH₂)₅CH₃ A-24 (±,±)CH(CH₃)CH(CH₃)CH₂CH₃ A-25 (±,R)CH(CH₃)CH(CH₃)CH₂CH₃A-26 (±,S)CH(CH₃)CH(CH₃)CH₂CH₃ A-27 (±)CH₂CH(CH₃)CF₃ A-28(R)CH₂CH(CH₃)CF₃ A-29 (S)CH₂CH(CH₃)CF₃ A-30 (±)CH₂CH(CF₃)CH₂CH₃ A-31(R)CH₂CH(CF₃)CH₂CH₃ A-32 (S)CH₂CH(CF₃)CH₂CH₃ A-33 (±,±)CH(CH₃)CH(CH₃)CF₃A-34 (±,R)CH(CH₃)CH(CH₃)CF₃ A-35 (±,S)CH(CH₃)CH(CH₃)CF₃ A-36(±,±)CH(CH₃)CH(CF₃)CH₂CH₃ A-37 (±,R)CH(CH₃)CH(CF₃)CH₂CH₃ A-38(±,S)CH(CH₃)CH(CF₃)CH₂CH₃ A-39 CF₃ A-40 CF₂CF₃ A-41 CF₂CF₂CF₃ A-42c-C₃H₅ A-43 (1-CH₃)-c-C₃H₄ A-44 c-C₅H₉ A-45 c-C₆H₁₁ A-46 (4-CH₃)-c-C₆H₁₀A-47 CH₂C(CH₃)═CH₂ A-48 CH₂CH₂C(CH₃)═CH₂ A-49 CH₂—C(CH₃)₃ A-50CH₂—Si(CH₃)₃ A-51 n-C₆H₁₃ A-52 (CH₂)₃—CH(CH₃)₂ A-53 (CH₂)₂—CH(CH₃)—C₂H₅A-54 CH₂—CH(CH₃)-n-C₃H₇ A-55 CH(CH₃)-n-C₄H₉ A-56 CH₂—CH(C₂H₅)₂ A-57CH(C₂H₅)-n-C₃H₇ A-58 CH₂-c-C₅H₉ A-59 CH₂—CH(CH₃)—CH(CH₃)₂ A-60CH(CH₃)—CH₂CH(CH₃)₂ A-61 CH(CH₃)—CH(CH₃)—C₂H₅ A-62 CH(CH₃)—C(CH₃)₃ A-63(CH₂)₂—C(CH₃)₃ A-64 CH₂—C(CH₃)₂—C₂H₅ A-65 2-CH₃-c-C₅H₈ A-66 3-CH₃-c-C₅H₈A-67 C(CH₃)₂-n-C₃H₇ A-68 (CH₂)₆—CH₃ A-69 (CH₂)₄—CH(CH₃)₂ A-70(CH₂)₃—CH(CH₃)—C₂H₅ A-71 (CH₂)₂—CH(CH₃)-n-C₃H₇ A-72 CH₂—CH(CH₃)-n-C₄H₉A-73 CH(CH₃)-n-C₅H₁₁ A-74 (CH₂)₃C(CH₃)₃ A-75 (CH₂)₂CH(CH₃)—CH(CH₃)₂ A-76(CH₂)CH(CH₃)—CH₂CH(CH₃)₂ A-77 CH(CH₃)(CH₂)₂—CH(CH₃)₂ A-78(CH₂)₂C(CH₃)₂C₂H₅ A-79 CH₂CH(CH₃)CH(CH₃)C₂H₅ A-80 CH(CH₃)CH₂CH(CH₃)C₂H₅A-81 CH₂C(CH₃)₂-n-C₃H₇ A-82 CH(CH₃)CH(CH₃)-n-C₃H₇ A-83 C(CH₃)₂-n-C₄H₉A-84 (CH₂)₂CH(C₂H₅)₂ A-85 CH₂CH(C₂H₅)-n-C₃H₇ A-86 CH(C₂H₅)-n-C₄H₉ A-87CH₂CH(CH₃)C(CH₃)₃ A-88 CH(CH₃)CH₂C(CH₃)₃ A-89 CH₂C(CH₃)₂CH(CH₃)₂ A-90CH₂CH(C₂H₅)CH(CH₃)₂ A-91 CH(CH₃)CH(CH₃)CH(CH₃)₂ A-92 C(CH₃)₂CH₂CH(CH₃)₂A-93 CH(C₂H₅)CH₂CH(CH₃)₂ A-94 CH(CH₃)C(CH₃)₂C₂H₅ A-95 CH(CH₃)CH(C₂H₅)₂A-96 C(CH₃)₂CH(CH₃)C₂H₅ A-97 CH(C₂H₅)CH(CH₃)C₂H₅ A-98C(CH₃)(C₂H₅)-n-C₃H₇ A-99 CH(n-C₃H₇)₂ A-100 CH(n-C₃H₇)CH(CH₃)₂ A-101C(CH₃)₂C(CH₃)₃ A-102 C(CH₃)(C₂H₅)—CH(CH₃)₂ A-103 C(C₂H₅)₃ A-104(3-CH₃)-c-C₆H₁₀ A-105 (2-CH₃)-c-C₆H₁₀ A-106 n-C₈H₁₇ A-107CH₂C(═NO—CH₃)CH₃ A-108 CH₂C(═NO—C₂H₅)CH₃ A-109 CH₂C(═NO-n-C₃H₇)CH₃ A-110CH₂C(═NO-i-C₃H₇)CH₃ A-111 CH(CH₃)C(═NOCH₃)CH₃ A-112 CH(CH₃)C(═NOC₂H₅)CH₃A-113 CH(CH₃)C(═NO-n-C₃H₇)CH₃ A-114 CH(CH₃)C(═NO-i-C₃H₇)CH₃ A-115C(═NOCH₃)C(═NOCH₃)CH₃ A-116 C(═NOCH₃)C(═NOC₂H₅)CH₃ A-117C(═NOCH₃)C(═NO-n-C₃H₇)CH₃ A-118 C(═NOCH₃)C(═NO-i-C₃H₇)CH₃ A-119C(═NOC₂H₅)C(═NOCH₃)CH₃ A-120 C(═NOC₂H₅)C(═NOC₂H₅)CH₃ A-121C(═NOC₂H₅)C(═NO-n-C₃H₇)CH₃ A-122 C(═NOC₂H₅)C(═NO-i-C₃H₇)CH₃ A-123CH₂C(═NO—CH₃)C₂H₅ A-124 CH₂C(═NO—C₂H₅)C₂H₅ A-125 CH₂C(═NO-n-C₃H₇)C₂H₅A-126 CH₂C(═NO-i-C₃H₇)C₂H₅ A-127 CH(CH₃)C(═NOCH₃)C₂H₅ A-128CH(CH₃)C(═NOC₂H₅)C₂H₅ A-129 CH(CH₃)C(═NO-n-C₃H₇)C₂H₅ A-130CH(CH₃)C(═NO-n-C₃H₇)C₂H₅ A-131 C(═NOCH₃)C(═NOCH₃)C₂H₅ A-132C(═NOCH₃)C(═NOC₂H₅)C₂H₅ A-133 C(═NOCH₃)C(═NO-n-C₃H₇)C₂H₅ A-134C(═NOCH₃)C(═NO-i-C₃H₇)C₂H₅ A-135 C(═NOC₂H₅)C(═NOCH₃)C₂H₅ A-136C(═NOC₂H₅)C(═NOC₂H₅)C₂H₅ A-137 C(═NOC₂H₅)C(═NO-n-C₃H₇)C₂H₅ A-138C(═NOC₂H₅)C(═NO-i-C₃H₇)C₂H₅ A-139 CH═CH—CH₂CH₃ A-140 CH₂—CH═CH—CH₃ A-141CH₂—CH₂—CH═CH₂ A-142 C(CH₃)₂CH₂CH₃ A-143 CH═C(CH₃)₂ A-144 C(═CH₂)—CH₂CH₃A-145 C(CH₃)═CH—CH₃ A-146 CH(CH₃)CH═CH₂ A-147 CH═CH-n-C₃H₇ A-148CH₂—CH═CH—C₂H₅ A-149 (CH₂)₂—CH═CH—CH₃ A-150 (CH₂)₃—CH═CH₂ A-151CH═CH—CH(CH₃)₂ A-152 CH₂—CH═C(CH₃)₂ A-153 (CH₂)₂—C(CH₃)═CH₂ A-154CH═C(CH₃)—C₂H₅ A-155 CH₂—C(═CH₂)—C₂H₅ A-156 CH₂—C(CH₃)═CH—CH₃ A-157CH₂—CH(CH₃)—CH═CH₂ A-158 C(═CH₂)—CH₂—CH₂—CH₃ A-159 C(CH₃)═CH—CH₂—CH₃A-160 CH(CH₃)—CH═CH—CH₃ A-161 CH(CH₃)—CH₂—CH═CH₂ A-162 C(═CH₂)CH(CH₃)₂A-163 C(CH₃)═C(CH₃)₂ A-164 CH(CH₃)—C(═CH₂)—CH₃ A-165 C(CH₃)₂—CH═CH₂A-166 C(C₂H₅)═CH—CH₃ A-167 CH(C₂H₅)—CH═CH₂ A-168 CH═CH—CH₂—CH₂—CH₂—CH₃A-169 CH₂—CH═CH—CH₂—CH₂—CH₃ A-170 CH₂—CH₂—CH═CH—CH₂—CH₃ A-171CH₂—CH₂—CH₂—CH═CH—CH₃ A-172 CH₂—CH₂—CH₂—CH₂—CH═CH₂ A-173CH═CH—CH₂—CH(CH₃)CH₃ A-174 CH₂—CH═CH—CH(CH₃)CH₃ A-175CH₂—CH₂—CH═C(CH₃)CH₃ A-176 CH₂—CH₂—CH₂—C(CH₃)═CH₂ A-177CH═CH—CH(CH₃)—CH₂—CH₃ A-178 CH₂—CH═C(CH₃)—CH₂—CH₃ A-179CH₂—CH₂—C(═CH₂)—CH₂—CH₃ A-180 CH₂—CH₂—C(CH₃)═CH—CH₃ A-181CH₂—CH₂—CH(CH₃)—CH═CH₂ A-182 CH═C(CH₃)—CH₂—CH₂—CH₃ A-183CH₂—C(═CH₂)—CH₂—CH₂—CH₃ A-184 CH₂—C(CH₃)═CH—CH₂—CH₃ A-185CH₂—CH(CH₃)—CH═CH—CH₃ A-186 CH₂—CH(CH₃)—CH₂—CH═CH₂ A-187C(═CH₂)—CH₂—CH₂—CH₂—CH₃ A-188 C(CH₃)═CH—CH₂—CH₂—CH₃ A-189CH(CH₃)—CH═CH—CH₂—CH₃ A-190 CH(CH₃)—CH₂—CH═CH—CH₃ A-191CH(CH₃)—CH₂—CH₂—CH═CH₂ A-192 CH═CH—C(CH₃)₃ A-193 CH═C(CH₃)—CH(CH₃)—CH₃A-194 CH₂—C(═CH₂)—CH(CH₃)—CH₃ A-195 CH₂—C(CH₃)═C(CH₃)—CH₃ A-196CH₂—CH(CH₃)—C(═CH₂)—CH₃ A-197 C(═CH₂)—CH₂—CH(CH₃)—CH₃ A-198C(CH₃)═CH—CH(CH₃)—CH₃ A-199 CH(CH₃)—CH═C(CH₃)—CH₃ A-200CH(CH₃)—CH₂—C(═CH₂)—CH₃ A-201 CH═C(CH₂—CH₃)—CH₂—CH₃ A-202CH₂—C(═CH—CH₃)—CH₂—CH₃ A-203 CH₂—CH(CH═CH₂)—CH₂—CH₃ A-204C(═CH—CH₃)—CH₂—CH₂—CH₃ A-205 CH(CH═CH₂)—CH₂—CH₂—CH₃ A-206C(CH₂—CH₃)═CH—CH₂—CH₃ A-207 CH(CH₂—CH₃)—CH═CH—CH₃ A-208CH(CH₂—CH₃)—CH₂—CH═CH₂ A-209 CH₂—C(CH₃)₂—CH═CH₂ A-210C(═CH₂)—CH(CH₃)—CH₂—CH₃ A-211 C(CH₃)═C(CH₃)—CH₂—CH₃ A-212CH(CH₃)—C(═CH₂)—CH₂—CH₃ A-213 CH(CH₃)—C(CH₃)═CH—CH₃ A-214CH(CH₃)—CH(CH₃)—CH═CH₂ A-215 C(CH₃)₂—CH═CH—CH₃ A-216 C(CH₃)₂—CH₂—CH═CH₂A-217 C(═CH₂)—C(CH₃)₃ A-218 C(═CH—CH₃)—CH(CH₃)—CH₃ A-219CH(CH═CH₂)—CH(CH₃)—CH₃ A-220 C(CH₂—CH₃)═C(CH₃)—CH₃ A-221CH(CH₂—CH₃)—C(═CH₂)—CH₃ A-222 C(CH₃)₂—C(═CH₂)—CH₃ A-223C(CH₃)(CH═CH₂)—CH₂—CH₃ A-224 C(CH₃)(CH₂CH₃)—CH₂—CH₂—CH₃ A-225CH(CH₂CH₃)—CH(CH₃)—CH₂—CH₃ A-226 CH(CH₂CH₃)—CH₂—CH(CH₃)—CH₃ A-227C(CH₃)₂—C(CH₃)₃ A-228 C(CH₂—CH₃)—C(CH₃)₃ A-229 C(CH₃)(CH₂—CH₃)—CH(CH₃)₂A-230 CH(CH(CH₃)₂)—CH(CH₃)₂ A-231 CH═CH—CH₂—CH₂—CH₂—CH₂—CH₃ A-232CH₂—CH═CH—CH₂—CH₂—CH₂—CH₃ A-233 CH₂—CH₂—CH═CH—CH₂—CH₂—CH₃ A-234CH₂—CH₂—CH₂—CH═CH—CH₂—CH₃ A-235 CH₂—CH₂—CH₂—CH₂—CH═CH—CH₃ A-236CH₂—CH₂—CH₂—CH₂—CH₂—CH═CH₂ A-237 CH═CH—CH₂—CH₂—CH(CH₃)—CH₃ A-238CH₂—CH═CH—CH₂—CH(CH₃)—CH₃ A-239 CH₂—CH₂—CH═CH—CH(CH₃)—CH₃ A-240CH₂—CH₂—CH₂—CH═C(CH₃)—CH₃ A-241 CH₂—CH₂—CH₂—CH₂—C(═CH₂)—CH₃ A-242CH═CH—CH₂—CH(CH₃)—CH₂—CH₃ A-243 CH₂—CH═CH—CH(CH₃)—CH₂—CH₃ A-244CH₂—CH₂—CH═C(CH₃)—CH₂—CH₃ A-245 CH₂—CH₂—CH₂—C(═CH₂)—CH₂—CH₃ A-246CH₂—CH₂—CH₂—C(CH₃)═CH—CH₃ A-247 CH₂—CH₂—CH₂—CH(CH₃)—CH═CH₂ A-248CH═CH—CH(CH₃)—CH₂—CH₂—CH₃ A-249 CH₂—CH═C(CH₃)—CH₂—CH₂—CH₃ A-250CH₂—CH₂—C(═CH₂)—CH₂—CH₂—CH₃ A-251 CH₂—CH₂—C(CH₃)═CH—CH₂—CH₃ A-252CH₂—CH₂—CH(CH₃)—CH═CH—CH₃ A-253 CH₂—CH₂—CH(CH₃)—CH₂—CH═CH₂ A-254CH═C(CH₃)—CH₂—CH₂—CH₂—CH₃ A-255 CH₂—C(═CH₂)—CH₂—CH₂—CH₂—CH₃ A-256CH₂—C(CH₃)═CH—CH₂—CH₂—CH₃ A-257 CH₂—CH(CH₃)—CH═CH—CH₂—CH₃ A-258CH₂—CH(CH₃)—CH₂—CH═CH—CH₃ A-259 CH₂—CH(CH₃)—CH₂—CH₂—CH═CH₂ A-260C(═CH₂)—CH₂—CH₂—CH₂—CH₂—CH₃ A-261 C(CH₃)═CH—CH₂—CH₂—CH₂—CH₃ A-262CH(CH₃)—CH═CH—CH₂—CH₂—CH₃ A-263 CH(CH₃)—CH₂—CH═CH—CH₂—CH₃ A-264CH(CH₃)—CH₂—CH₂—CH═CH—CH₃ A-265 CH(CH₃)—CH₂—CH₂—CH₂—CH═CH₂ A-266CH═CH—CH₂—C(CH₃)₃ A-267 CH₂—CH═CH—C(CH₃)₃ A-268 CH═CH—CH(CH₃)—CH(CH₃)₂A-269 CH₂—CH═C(CH₃)—CH(CH₃)₂ A-270 CH₂—CH₂—C(═CH₂)—CH(CH₃)₂ A-271CH₂—CH₂—C(CH₃)═C(CH₃)₂ A-272 CH₂—CH₂—CH(CH₃)—C(═CH₂)—CH₃ A-273CH═C(CH₃)—CH₂—CH(CH₃)₂ A-274 CH₂—C(═CH₂)—CH₂—CH(CH₃)₂ A-275CH₂—C(CH₃)═CH—CH(CH₃)₂ A-276 CH₂—CH(CH₃)—CH═C(CH₃)₂ A-277CH₂—CH(CH₃)—CH₂—C(═CH₂)—CH₃ A-278 C(═CH₂)—CH₂—CH₂—CH(CH₃)₂ A-279C(CH₃)═CH—CH₂—CH(CH₃)₂ A-280 CH(CH₃)—CH═CH—CH(CH₃)₂ A-281CH(CH₃)—CH₂—CH═C(CH₃)₂ A-282 CH(CH₃)—CH₂—CH₂—C(═CH₂)—CH₃ A-283CH═CH—C(CH₃)₂—CH₂—CH₃ A-284 CH₂—CH₂—C(CH₃)₂—CH═CH₂ A-285CH═C(CH₃)—CH(CH₃)—CH₂—CH₃ A-286 CH₂—C(═CH₂)—CH(CH₃)—CH₂—CH₃ A-287CH₂—C(CH₃)═C(CH₃)—CH₂—CH₃ A-288 CH₂—CH(CH₃)—C(═CH₂)—CH₂—CH₃ A-289CH₂—CH(CH₃)—C(CH₃)═CH—CH₃ A-290 CH₂—CH(CH₃)—CH(CH₃)—CH═CH₂ A-291C(═CH₂)—CH₂—CH(CH₃)—CH₂—CH₃ A-292 C(CH₃)═CH—CH(CH₃)—CH₂—CH₃ A-293CH(CH₃)—CH═C(CH₃)—CH₂—CH₃ A-294 CH(CH₃)—CH₂—C(═CH₂)—CH₂—CH₃ A-295CH(CH₃)—CH₂—C(CH₃)═CH—CH₃ A-296 CH(CH₃)—CH₂—CH(CH₃)—CH═CH₂ A-297CH₂—C(CH₃)₂—CH═CH—CH₃ A-298 CH₂—C(CH₃)₂—CH₂—CH═CH₂ A-299C(═CH₂)—CH(CH₃)—CH₂—CH₂—CH₃ A-300 C(CH₃)═C(CH₃)—CH₂—CH₂—CH₃ A-301CH(CH₃)—C(═CH₂)—CH₂—CH₂—CH₃ A-302 CH(CH₃)—C(CH₃)═CH—CH₂—CH₃ A-303CH(CH₃)—CH(CH₃)—CH═CH—CH₃ A-304 CH(CH₃)—CH(CH₃)—CH₂—CH═CH₂ A-305C(CH₃)₂—CH═CH—CH₂—CH₃ A-306 C(CH₃)₂—CH₂—CH═CH—CH₃ A-307C(CH₃)₂—CH₂—CH₂—CH═CH₂ A-308 CH═CH—CH(CH₂—CH₃)—CH₂—CH₃ A-309CH₂—CH═C(CH₂—CH₃)—CH₂—CH₃ A-310 CH₂—CH₂—C(═CH—CH₃)—CH₂—CH₃ A-311CH₂—CH₂—CH(CH═CH₂)—CH₂—CH₃ A-312 CH═C(CH₂—CH₃)—CH₂—CH₂—CH₃ A-313CH₂—C(═CH—CH₃)—CH₂—CH₂—CH₃ A-314 CH₂—CH(CH═CH₂)—CH₂—CH₂—CH₃ A-315CH₂—C(CH₂—CH₃)═CH—CH₂—CH₃ A-316 CH₂—CH(CH₂—CH₃)—CH═CH—CH₃ A-317CH₂—CH(CH₂—CH₃)—CH—CH═CH₂ A-318 C(═CH—CH₃)—CH₂—CH₂—CH₂—CH₃ A-319CH(CH═CH₂)—CH₂—CH₂—CH₂—CH₃ A-320 C(CH₂—CH₃)═CH—CH₂—CH₂—CH₃ A-321CH(CH₂—CH₃)—CH═CH—CH₂—CH₃ A-322 CH(CH₂—CH₃)—CH₂—CH═CH—CH₃ A-323CH(CH₂—CH₃)—CH₂—CH₂—CH═CH₂ A-324 C(═CH—CH₂—CH₃)—CH₂—CH₂—CH₃ A-325C(CH═CH—CH₃)—CH₂—CH₂—CH₃ A-326 C(CH₂—CH═CH₂)—CH₂—CH₂—CH₃ A-327CH═C(CH₃)—C(CH₃)₃ A-328 CH₂—C(═CH₂)—C(CH₃)₃ A-329CH₂—C(CH₃)₂—CH(═CH₂)—CH₃ A-330 C(═CH₂)—CH(CH₃)—CH(CH₃)—CH₃ A-331C(CH₃)═C(CH₃)—CH(CH₃)—CH₃ A-332 CH(CH₃)—C(═CH₂)—CH(CH₃)—CH₃ A-333CH(CH₃)—C(CH₃)═C(CH₃)—CH₃ A-334 CH(CH₃)—CH(CH₃)—C(CH₂)—CH₃ A-335C(CH₃)₂—CH═C(CH₃)—CH₃ A-336 C(CH₃)₂—CH₂—C(═CH₂)—CH₃ A-337C(CH₃)₂—C(═CH₂)—CH₂—CH₃ A-338 C(CH₃)₂—C(CH₃)═CH—CH₃ A-339C(CH₃)₂—CH(CH₃)CH═CH₂ A-340 CH(CH₂—CH₃)—CH₂—CH(CH₃)—CH₃ A-341CH(CH₂—CH₃)—CH(CH₃)—CH₂—CH₃ A-342 C(CH₃)(CH₂—CH₃)—CH₂—CH₂—CH₃ A-343CH(i-C₃H₇)—CH₂—CH₂—CH₃ A-344 CH═C(CH₂—CH₃)—CH(CH₃)—CH₃ A-345CH₂—C(═CH—CH₃)—CH(CH₃)—CH₃ A-346 CH₂—CH(CH═CH₂)—CH(CH₃)—CH₃ A-347CH₂—C(CH₂—CH₃)═C(CH₃)—CH₃ A-348 CH₂—CH(CH₂—CH₃)—C(═CH₂)—CH₃ A-349CH₂—C(CH₃)(CH═CH₂)—CH₂—CH₃ A-350 C(═CH₂)—CH(CH₂—CH₃)—CH₂—CH₃ A-351C(CH₃)═C(CH₂—CH₃)—CH₂—CH₃ A-352 CH(CH₃)—C(═CH—CH₃)—CH₂—CH₃ A-353CH(CH₃)—CH(CH═CH₂)—CH₂—CH₃ A-354 CH═C(CH₂—CH₃)—CH(CH₃)—CH₃ A-355CH₂—C(═CH—CH₃)—CH(CH₃)—CH₃ A-356 CH₂—CH(CH═CH₂)—CH(CH₃)—CH₃ A-357CH₂—C(CH₂—CH₃)═C(CH₃)—CH₃ A-358 CH₂—CH(CH₂—CH₃)—C(═CH₂)—CH₃ A-359C(═CH—CH₃)—CH₂—CH(CH₃)—CH₃ A-360 CH(CH═CH₂)—CH₂—CH(CH₃)—CH₃ A-361C(CH₂—CH₃)═CH—CH(CH₃)—CH₃ A-362 CH(CH₂—CH₃)CH═C(CH₃)—CH₃ A-363CH(CH₂—CH₃)CH₂—C(═CH₂)—CH₃ A-364 C(═CH—CH₃)CH(CH₃)—CH₂—CH₃ A-365CH(CH═CH₂)CH(CH₃)—CH₂—CH₃ A-366 C(CH₂—CH₃)═C(CH₃)—CH₂—CH₃ A-367CH(CH₂—CH₃)—C(═CH₂)—CH₂—CH₃ A-368 CH(CH₂—CH₃)—C(CH₃)═CH—CH₃ A-369CH(CH₂—CH₃)—CH(CH₃)—CH═CH₂ A-370 C(CH₃)(CH═CH₂)—CH₂—CH₂—CH₃ A-371C(CH₃)(CH₂—CH₃)—CH═CH—CH₃ A-372 C(CH₃)(CH₂—CH₃)—CH₂—CH═CH₂ A-373C[═C(CH₃)—CH₃]—CH₂—CH₂—CH₃ A-374 CH[C(═CH₂)—CH₃]—CH₂—CH₂—CH₃ A-375C(i-C₃H₇)═CH—CH₂—CH₃ A-376 CH(i-C₃H₇)—CH═CH—CH₃ A-377CH(i-C₃H₇)—CH₂—CH═CH₂ A-378 C(═CH—CH₃)—C(CH₃)₃ A-379 CH(CH═CH₂)—C(CH₃)₃A-380 C(CH₃)(CH═CH₂)CH(CH₃)—CH₃ A-381 C(CH₃)(CH₂—CH₃)C(═CH₂)—CH₃ A-3822-CH₃-cyclohex-1-enyl A-383 [2-(═CH₂)]-c-C₆H₉ A-3842-CH₃-cyclohex-2-enyl A-385 2-CH₃-cyclohex-3-enyl A-3862-CH₃-cyclohex-4-enyl A-387 2-CH₃-cyclohex-5-enyl A-3882-CH₃-cyclohex-6-enyl A-389 3-CH₃-cyclohex-1-enyl A-3903-CH₃-cyclohex-2-enyl A-391 [3-(═CH₂)]-c-C₆H₉ A-3923-CH₃-cyclohex-3-enyl A-393 3-CH₃-cyclohex-4-enyl A-3943-CH₃-cyclohex-5-enyl A-395 3-CH₃-cyclohex-6-enyl A-3964-CH₃-cyclohex-1-enyl A-397 4-CH₃-cyclohex-2-enyl A-3984-CH₃-cyclohex-3-enyl A-399 [4-(═CH₂)]-c-C₆H₉

The compounds I are suitable as fungicides. They are distinguishedthrough an outstanding effectiveness against a broad spectrum ofphytopathogenic fungi, especially from the classes of the Ascomycetes,Deuteromycetes, Oomycetes and Basidiomycetes. Some are systemicallyeffective and they can be used in plant protection as foliar and soilfungicides.

They are particularly important in the control of a multitude of fungion various cultivated plants, such as wheat, rye, barley, oats, rice,maize, grass, bananas, cotton, soya, coffee, sugar cane, vines, fruitsand ornamental plants, and vegetables, such as cucumbers, beans,tomatoes, potatoes and cucurbits, and on the seeds of these plants.

-   -   They are especially suitable for controlling the following plant        diseases:    -   Alternaria species on fruit and vegetables,    -   Bipolaris and Drechslera species on cereals, rice and lawns,    -   Blumeria graminis (powdery mildew) on cereals,    -   Botrytis cinerea (gray mold) on strawberries, vegetables,        ornamental plants and grapevines,    -   Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,    -   Fusarium and Verticillium species on various plants,    -   Mycosphaerella species on bananas and peanuts,    -   Phytophthora infestans on potatoes and tomatoes,    -   Plasmopara viticola on grapevines,    -   Podosphaera leucotricha on apples,    -   Pseudocercosporella herpotrichoides on wheat and barley,    -   Pseudoperonospora species on hops and cucumbers,    -   Puccinia species on cereals,    -   Pyricularia oryzae on rice,    -   Rhizoctonia species on cotton, rice and lawns,    -   Septoria tritici and Stagonospora nodorum on wheat,    -   Uncinula necator on grapevines,    -   Ustilago species on cereals and sugar cane, and    -   Venturia species (scab) on apples and pears.

The compounds I are also suitable for controlling harmful fungi, such asPaecilomyces variotii, in the protection of materials (e.g. wood, paper,paint dispersions, fibers or fabrics) and in the protection of storedproducts.

The compounds I are employed by treating the fungi or the plants, seeds,materials or soil to be protected from fungal attack with a fungicidallyeffective amount of the active compounds. The application can be carriedout both before and after the infection of the materials, plants orseeds by the fungi.

The fungicidal compositions generally comprise between 0.1 and 95%,preferably between 0.5 and 90%, by weight of active compound.

When employed in plant protection, the amounts applied are, depending onthe kind of effect desired, between 0.01 and 2.0 kg of active compoundper ha.

In seed treatment, amounts of active compound of 0.001 to 0.1 g,preferably 0.01 to 0.05 g, per kilogram of seed are generally necessary.

When used in the protection of materials or stored products, the amountof active compound applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg,of active compound per cubic meter of treated material.

The compounds I can be converted to the usual formulations, e.g.solutions, emulsions, suspensions, dusts, powders, pastes and granules.The application form depends on the respective intended use; it shouldin any case guarantee a fine and uniform distribution of the compoundaccording to the invention.

The formulations are prepared in a known way, e.g. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants, it being possible, when water is thediluent, also to use other organic solvents as auxiliary solvents.Suitable auxiliaries for this purpose are essentially: solvents, such asaromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes),paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol),ketones (e.g. cyclohexanone), amines (e.g. ethanolamine,dimethylformamide) and water; carriers, such as ground natural minerals(e.g. kaolins, clays, talc, chalk) and ground synthetic ores (e.g.highly dispersed silicic acid, silicates); emulsifiers, such as nonionicand anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers,alkylsulfonates and arylsulfonates) and dispersants, such aslignosulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammoniumsalts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonicacid and dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids, andalkali metal and alkaline earth metal salts thereof, salts of sulfatedfatty alcohol glycol ethers, condensation products of sulfonatednaphthalene and naphthalene derivatives with formaldehyde, condensationproducts of naphthalene or of naphthalenesulfonic acid with phenol andformaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, octylphenol and nonylphenol, alkylphenol polyglycolethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylatedpolyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitolesters, lignosulfite waste liquors and methylcellulose.

Petroleum fractions having medium to high boiling points, such askerosene or diesel fuel, furthermore coal tar oils, and oils ofvegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons,e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene,alkylated naphthalenes or derivatives thereof, methanol, ethanol,propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol,cyclohexanone, chlorobenzene or isophorone, or highly polar solvents,e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone orwater, are suitable for the preparation of directly sprayable solutions,emulsions, pastes or oil dispersions.

Powders, preparations for broadcasting and dusts can be prepared bymixing or grinding together the active substances with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are, e.g., mineral earths, such as silica gels,silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such as, e.g.,ammonium sulfate, ammonium phosphate, ammonium nitrate or ureas, andplant products, such as cereal meal, tree bark meal, wood meal andnutshell meal, cellulose powders and other solid carriers.

The formulations generally comprise between 0.01 and 95% by weight,preferably between 0.1 and 90% by weight, of the active compound. Theactive compounds are employed therein in a purity of 90% to 100%,preferably 95% to 100% (according to the NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention areintimately mixed with 95 parts by weight of finely divided kaolin. Inthis way, a dust comprising 5% by weight of the active compound isobtained.

II. 30 parts by weight of a compound according to the invention areintimately mixed with a mixture of 92 parts by weight of pulverulentsilica gel and 8 parts by weight of liquid paraffin, which had beensprayed onto the surface of this silica gel. In this way, an activecompound preparation with good adhesive properties (active compoundcontent 23% by weight) is obtained.

III. 10 parts by weight of a compound according to the invention aredissolved in a mixture consisting of 90 parts by weight of xylene, 6parts by weight of the addition product of 8 to 10 mol of ethylene oxidewith 1 mol of the N-monoethanolamide of oleic acid, 2 parts by weight ofthe calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight ofthe addition product of 40 mol of ethylene oxide with 1 mol of castoroil (active compound content 9% by weight).

IV. 20 parts by weight of a compound according to the invention aredissolved in a mixture consisting of 60 parts by weight ofcyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight ofthe addition product of 7 mol of ethylene oxide with 1 mol ofisooctylphenol and 5 parts by weight of the addition product of 40 molof ethylene oxide with 1 mol of castor oil (active compound content 16%by weight).

V. 80 parts by weight of a compound according to the invention arethoroughly mixed with 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 7 parts byweight of pulverulent silica gel and are ground in a hammer mill (activecompound content 80% by weight).

VI. 90 parts by weight of a compound according to the invention aremixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solutionis obtained which is suitable for use in the form of very small drops(active compound content 90% by weight).

VII. 20 parts by weight of a compound according to the invention aredissolved in a mixture consisting of 40 parts by weight ofcyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight ofthe addition product of 7 mol of ethylene oxide with 1 mol ofisooctylphenol and 10 parts by weight of the addition product of 40 molof ethylene oxide with 1 mol of castor oil. By running the solution into100 000 parts by weight of water and finely dispersing it therein, anaqueous dispersion is obtained comprising 0.02% by weight of the activecompound.

VIII. 20 parts by weight of a compound according to the invention arethoroughly mixed with 3 parts by weight of the sodium salt ofdiisobutyinaphthalene-α-sulfonic acid, 17 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel and are ground in a hammer mill. Aspray emulsion comprising 0.1% by weight of the active compound isobtained by fine dispersion of the mixture in 20 000 parts by weight ofwater.

The active compounds can be used as such, in the form of theirformulations or of the application forms prepared therefrom, e.g. in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, preparations forbroadcasting or granules, by spraying, atomizing, dusting, broadcastingor watering. The application forms depend entirely on the intended uses;they should always ensure the finest possible dispersion of the activecompounds according to the invention.

Aqueous application forms can be prepared from emulsifiableconcentrates, pastes or wettable powders (spray powders, oildispersions) by addition of water. To prepare emulsions, pastes or oildispersions, the substances can be homogenized in water, as such ordissolved in an oil or solvent, by means of wetting agents, tackifiers,dispersants or emulsifiers. However, it is also possible to prepareconcentrates comprising active substance, wetting agent, tackifier,dispersant or emulsifier and possibly solvent or oil which are suitablefor dilution with water.

The concentrations of active compound in the ready-for-use preparationscan be varied within relatively wide ranges. In general, they arebetween 0.0001 and 10%, preferably between 0.01 and 1%.

The active compounds can also be used with great success in theultra-low volume (ULV) process, it being possible to apply formulationswith more than 95% by weight of active compound or even the activecompound without additives.

Oils of various types, herbicides, fungicides, other pesticides andbactericides can be added to the active compounds, if need be also notuntil immediately before use (tank mix). These agents can be added tothe preparations according to the invention in a weight ratio of 1:10 to10:1.

The preparations according to the invention can, in the application formas fungicides, also be present together with other active compounds,e.g. with herbicides, insecticides, growth regulators, fungicides oralso with fertilizers. On mixing the compounds I or the preparationscomprising them in the application form as fungicides with otherfungicides, in many cases an expansion of the fungicidal spectrum ofactivity is obtained.

The following lists of fungicides, with which the compounds-according tothe invention can be used in conjunction, is intended to illustrate thepossible combinations but does not limit them:

-   -   acylalanines, such as benalaxyl, metalaxyl, ofurace or oxadixyl,    -   amine derivatives, such as aldimorph, dodine, dodemorph,        fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine        or tridemorph,    -   anilinopyrimidine, such as pyrimethanil, mepanipyrim or        cyprodinyl,    -   antibiotics, such as cycloheximide, griseofulvin, kasugamycin,        natamycin, polyoxin or streptomycin,    -   azoles, such as bitertanol, bromoconazole, cyproconazole,        difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole,        fluquinconazole, flusilazole, hexaconazole, imazalil,        metconazole, myclobutanil, penconazole, propiconazole,        prochloraz, prothioconazole, tebuconazole, triadimefon,        triadimenol, flutriafol, triflumizole or triticonazole,    -   dicarboximides, such as iprodione, myclozolin, procymidone or        vinclozolin,    -   dithiocarbamates, such as ferbam, nabam, maneb, mancozeb, metam,        metiram, propineb, polycarbamate, thiram, ziram or zineb,    -   heterocyclic compounds, such as anilazine, benomyl, boscalid,        carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet,        dithianon, famoxadone, fenamidone, fenarimol, fuberidazole,        flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol,        probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen,        silthiofam, thiabendazole, thifluzamide, thiophanate-methyl,        tiadinil, tricyclazole or triforine,    -   copper fungicides, such as Bordeaux mixture, copper acetate,        copper oxychloride or basic copper sulfate,    -   nitrophenyl derivatives, such as binapacryl, dinocap, dinobuton        or nitrophthal-isopropyl,    -   phenylpyrroles, such as fenpiclonil or fludioxonil,    -   sulfur,    -   other fungicides, such as acibenzolar-S-methyl, benthiavalicarb,        carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet,        diclomezine, diclocymet, diethofencarb, edifenphos, ethaboxam,        fenhexamid, fentin acetate, fenoxanil, ferimzone, fluazinam,        fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene,        metrafenone, pencycuron, propamocarb, phthalide,        tolclofos-methyl, quintozene or zoxamide,    -   strobilurins, such as azoxystrobin, dimoxystrobin,        fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,        picoxystrobin, pyraclostrobin or trifloxystrobin,    -   sulfenic acid derivatives, such as captafol, captan,        dichlofluanid, folpet or tolylfluanid,    -   cinnamides and analogous compounds, such as dimethomorph,        flumetover or flumorph.

SYNTHESIS EXAMPLES

The procedures described in the following synthesis examples were usedto prepare further compounds I by appropriate modification of thestarting compounds. The compounds thus obtained are listed in thefollowing tables, together with physical data.

1.) Synthesis of2-cyano4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine1.1.) 2-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-chloropyrimidine

50 ml of methylmagnesium bromide solution (3 M in tetrahydrofuran) wasadded dropwise to a mixture of 32.5 g (0.1 mol) of1-methylthio-4,6-dichloro-5-(2,4,6-trifluorophenyl)pyrimidine (WO02/74753) and 0.5 g of bisdiphenylphosphinoferrocenepalladium dichloridein 150 ml of tetrahydrofuran p.a., and during the addition the reactiontemperature increased to about 40° C. The reaction mixture was stirredat room temperature overnight, and saturated ammonium chloride solutionwas then added. The aqueous phase was extracted with methyl t-butylether and the combined organic phases were concentrated. The residue waspurified first by chromatography using cyclohexane/methyl t-butyl ether9:1 on silica gel and then by preparative MPLC on RP-18 silica gel. Thisgave 18.8 g (62%) of the title compound as a white solid.

¹H-NMR (CDCl₃, δ in ppm): 6.8 (t, 2H); 2.6 (s, 3H); 2.3 (s, 3H)

1.2.)2-Methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine

At 50° C., 70 ml (0.035 mol) of a 0.5 M solution of2-methylbutylmagnesium bromide (in tetrahydrofuran) were added to 9.1 g(30 mmol) of2-methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-chloropyrimidine(Example 1.1.) and about 200 mg ofbisdiphenylphosphinoferrocenepalladium dichloride in 90 ml of toluene.After about 2 hours, an additional about 200 mg ofbisdiphenylphosphinoferrocenepalladium dichloride and, a little at atime, a further 50 ml of a 0.5 M solution of 2-methylbutyl-magnesiumbromide (in tetrahydrofuran) were added. The reaction was monitored byHPLC.

The mixture was then hydrolyzed using saturated ammonium chloridesolution, and the aqueous phase was extracted with methyl t-butyl ether.The combined organic phases were concentrated and the residue waspurified by column chromatography on silica gel using cyclohexane/methylt-butyl ether 9:1 and preparative MPLC on RP-18 silica gel. This gave5.9 g (58%) of the title compound as a colorless oil.

¹H-NMR (CDCl₃, δ in ppm): 6.8 (t, 2H); 2.6 (s, 3H); 2.45 (dd, 1H); 2.2(s, 3H); 2.15 (dd, 1H); 1.9 (m, 1H); 1.25 (m, 1H); 1.05 (m, 1H); 0.8 (m,6H)

1.3.)2-Methylsulfonyl-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine

At 0° C., 2.8 g (12.3 mmol) of m-chloroperbenzoic acid (purity 77%) wereadded a little at a time to a solution of 1.9 g (5.6 mmol) of2-methylthio-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine(Example 1.2.) in 20 ml of methylene chloride p.a., and the mixture wasstirred at room temperature overnight. The reaction mixture was thenapplied directly to a silica gel column and eluted withcyclohexane/methyl t-butyl ether 7:3. This gave 1.4 g (67%) of the titlecompound as a light-yellow oil.

¹H-NMR (CDCl₃, δ in ppm): 6.9 (t, 2H); 3.4 (s, 3H); 2.65 (dd, 1H); 2.45(s, 3H); 2.4 (dd, 1H); 1.9 (m, 1H); 1.3 (m, 1H); 1.1 (m, 1H)

1.4.)2-Cyano-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine

A mixture of 0.4 g (1 mmol) of2-methylsulfonyl-4-methyl-5-(2,4,6-trifluorophenyl)-6-(2-methylbutyl)pyrimidine(Example 1.3.) and 0.2 g (3 mmol) of potassium cyanide in 20 ml ofacetonitrile p.a. was stirred at 20° C. for about 16 hours. The reactionmixture was then concentrated, the residue was taken up in methylenechloride and the organic phase was extracted with water. The organicphase was concentrated and the residue was purified by columnchromatography using cyclohexane/methyl t-butyl ether mixtures. Thisgave 0.3 g (94%) of the title compound as a colorless oil.

¹H-NMR (CDCl₃, δ in ppm): 6.9 (m, 2H); 2.6 (dd, 1H); 2.4 (s, 3H); 2.3(dd, 1H); 1.9 (m, 1H); 1.25 (m, 1H); 1.1 (m, 1H); 0.75 (m, 6H)

TABLE I

Physical data m.p. (° C.), IR (cm⁻¹) or No. R¹ R² R³ L_(n) NMR (ppm) I-12-methyl- chloro cyano 2,4,6-F₃ 6.9(t, 2H); 2.7(dd, butyl 1H), 2.4(dd,1H); 1.9(m, 1H); 1.25 (m, 1H); 1.15(m, 1H); 0.8(m, 6H) I-2 2-methyl-cyano cyano 2,4,6-F₃ 6.95(t, 2H); 2.8 butyl (dd, 1H); 2.5(dd, 1H);1.95(m, 1H); 1.25(m, 1H); 1.15 (m, 1H); 0.8(m, 6H) I-3 cyclohexyl cyanocyano 2,4,6-F₃ 153° C. I-4 2-methyl- methyl cyano 2,4,6-F₃ 6.9(m, 2H);2.6 butyl (dd, 1H); 2.4 (s, 3H); 2.3(dd, 1H); 1.9(m, 1H); 1.25(m, 1H);1.1 (m, 1H); 0.75 (m, 6H) I-5 but-3-enyl methyl cyano 2,4,6-F₃ 6.9(t,2H); 5.9(m, 1H); 5.1(d, 1H); 5.0(d, 1H); 3.15 (t, 2H); 2.65(m, 2H);2.5(s, 3H) I-6 2-methyl- methyl C(═S)NH₂ 2,4,6-F₃ 37-41 butyl I-72-methyl- methyl C(═S)NH₂ 2,4,6-F₃ 45-51 butyl

Examples of the Action Against Harmful Fungi

The fungicidal action of the compounds of the formula I was demonstratedby the following experiments:

The active compounds were prepared as a stock solution with 0.25% byweight of active compound in acetone or DMSO. 1% by weight of theemulsifier Uniperol® EL (wetting agent having emulsifying and dispersingaction based on ethoxylated alkylphenols) was added to this solution,and the solution was diluted with water to the desired concentration.

Use Examples

1. Activity against early blight of tomato caused by Alternaria solani,protective application

Leaves of potted plants of the cultivar “Groβe Fleischtomate St. Pierre”were sprayed to runoff point with an aqueous suspension of the activecompound concentration given below. The next day, the leaves wereinfected with an aqueous spore suspension of Alternaria solani in 2%biomalt solution with a concentration of 0.17×10⁶ spores/ml. The plantswere then placed in a water-vapor-saturated chamber at temperaturesbetween 20 and 22° C. After 5 days, the early blight on the untreatedbut infected control plants had developed to such an extent that theinfection could be determined visually in %.

The plants which had been treated with 250 ppm of the active compoundsI-1, I-2, I-6 and I-7 showed less than 5% infection. The untreatedcontrol plants showed an infection of 80%.

2. Activity against gray mold on capsicum leaves caused by Botrytiscinerea, protective application

Capsicum seedlings of the cultivar “Neusiedler Ideal Elite” were, after4-5 leaves had fully developed, sprayed to runoff point with an aqueoussuspension of the active compound concentration given below. The nextday, the treated plants were inoculated with a spore suspension ofBotrytis cinerea comprising 1.7×10⁶ spores/ml in a 2% aqueous biomaltsolution. The test plants were subsequently placed in a climatizedchamber at 22 to 24° C. and high atmospheric humidity. After 5 days, theextent of the fungal infection on the leaves could be determinedvisually in %.

The plants which had been treated with 250 ppm of the active compoundsI-1 and I-4 showed no infection. The untreated control plants showed aninfection of 90%.

3. Activity against mildew on cucumber leaves caused by Sphaerothecafuliginea, protective application

Leaves of potted cucumber seedlings of the cultivar “Chinese snake”were, at the cotyledon stage, sprayed to runoff point with an aqueoussuspension of the active compound concentration given below. 20 hoursafter the spray coating had dried on, the plants were inoculated with anaqueous spore suspension of mildew of cucumber (Sphaerotheca fuliginea).The plants were then cultivated in a greenhouse at temperatures between20 and 24° C. and 60 to 80% relative atmospheric humidity for 7 days.The extend of the mildew development was then determined visually in %infection of the coltyledon area.

The plants which had been treated with 250 ppm of the active compoundsI-2 and I-4 showed no infection. The untreated control plants showed aninfection of 90%.

1. A 2-substituted pyrimidine of the formula I

in which the index and the substituents are as defined below: n is aninteger from 1 to 5, where at least one substituent L is located in theortho-position on the phenyl ring; L is halogen, cyano, cyanato (OCN),C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₆-alkoxy,C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═O)-A,—C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)—C(═O)-A,N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A, S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A, m is0, 1 or 2; A, A′, A″ independently of one another are hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkenyl, phenyl, where the organic radicals may be partiallyor fully halogenated or may be substituted by cyano or C₁-C₄-alkoxy; orA and A′ together with the atoms to which they are attached are a five-or six-membered saturated, partially unsaturated or aromatic heterocyclewhich contains one to four heteroatoms from the group consisting of O, Nand S; R¹ is C₃-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₃-C₁₀-alkynyl,C₃-C₁₂-cycloalkyl, C₃-C₁₀-cycloalkenyl or a five- to ten-memberedsaturated, partially unsaturated or aromatic heterocycle which isattached via carbon and contains one to four heteroatoms from the groupconsisting of O, N and S, R² is halogen, cyano, C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy orC₃-C₄-alkynyloxy, where the alkyl, alkenyl and alkynyl radicals of R²may be substituted by halogen, cyano, nitro, C₁-C₂-alkoxy orC₁-C₄-alkoxycarbonyl, where the aliphatic, alicyclic or aromatic groupsof the radical definitions of L, R¹ and/or R² for their part may bepartially or fully halogenated or may carry one to four groups R^(u):R^(u) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═O)-A,—C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′) —C(═O)-A,N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A, S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A,where m, A, A′, A″ are as defined above and where the aliphatic,alicyclic or aromatic groups for their part may be partially or fullyhalogenated or may carry one to three groups R^(v), R^(v) having thesame meaning as R^(u); R³ is cyano, CO₂R^(a), C(═O)NR^(z)R^(b),C(═O)—N—OR^(b), C(═NOR^(a))NR^(z)R^(b), C(═NR^(a))NR^(z)R^(b),C(═O)NR^(a)—NR^(z)R^(b), C(═N—NR^(z)R^(c))NR^(a)R^(b), C(═O)R^(a),C(═NOR^(b))R^(a), C(═N—NR^(z)R^(b))R^(a), CR^(a)R^(b)—OR^(z),CR^(a)R^(b)—NR^(z)R^(c), ON(═CR^(a)R^(b)), O—C(═O)R^(a), NR^(a)R^(b′),NR^(a)(C(═O)R^(b)), NR^(a)(C(═O)OR^(b)), NR^(a)(C(═O)—NR^(z)R^(b)),NR^(a)(C(═NR^(c))R^(b)), NR^(a)(N═CR^(c)R^(b)), NR^(a)—NR^(z)R^(b),NR^(z)—OR^(a), NR^(a)(C(═NR^(c))—NR^(z)R^(b)), NR^(a)(C(═NOR^(c))R^(b));where R^(a), R^(b), R^(c) independently of one another are hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl orC₄-C₆-cycloalkenyl; R^(b′) has the same meanings as R^(b), except forhydrogen; R^(z) has the same meanings as R^(a) and may additionally be—CO—R^(a); where the aliphatic or alicyclic groups of the radicaldefinitions of R^(a),R^(b),R^(c) or R^(z) for their part may bepartially or fully halogenated or may carry one to four groups R^(w):R^(w) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, and wheretwo of the radicals R^(a), R^(b), R^(c) or R^(z) together with the atomsto which they are attached may form a five- or six-membered saturated,partially unsaturated or aromatic heterocycle which contains one to fourheteroatoms from the group consisting of O, N and S.
 2. A 2-substitutedpyrimidine according to claim 1 where R² is chlorine, cyano, methyl,ethyl or methoxy.
 3. A 2-substituted pyrimidine according to claim 1where R³ is cyano, C(═O)NR^(z)R^(b), C(═NOR^(a))NR^(z)R^(b),C(═NOR^(b))R^(a), C(═N—NR^(z)R^(b)) R^(a) or CR^(a)R^(b)—NR^(z)R^(c). 4.A 2-substituted pyrimidine according to claim 1 where R³ isON(═CR^(a)R^(b)), NR^(a)(C(═O)R^(b)), NR^(a)(C(═O)OR^(b)),NR^(a)(N═CR^(c)R^(b)) or NR^(z)—OR^(a).
 5. A 2-substituted pyrimidineaccording to claim 1 in which the phenyl group substituted by L_(n) isthe group B

where # is the point of attachment to the pyrimidine skeleton and L¹ isfluorine, chlorine, CH₃ or CF₃; L², L⁴ independently of one another arehydrogen, CH₃ or fluorine; L³ is hydrogen, fluorine, chlorine, cyano,CH₃, SCH₃, OCH₃, SO₂CH₃, NH—C(═O)CH₃, N(CH₃)—C(═O)CH₃ or COOCH₃ and L⁵is hydrogen, fluorine, chlorine or CH₃.
 6. A process for preparing2-substituted pyrimidines of the formula I according

to claim 1 where R³ is cyano, which comprises reacting a compound of theformula III, in which the substituents L, R¹ and R² are as defined inclaim 1 and X is halogen, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulfoxyl, C₁-C₆-alkylsulfonyl or C₁-C₆-alkylsulfenyl with ahydrocyannic acid derivative, if appropriate in the presence of a base.7. A composition suitable for controlling harmful fungi which comprisesa solid or liquid carrier and a compound of the formula I according toclaim
 1. 8. A method for controlling phytopathogenic harmful fungi whichcomprises treating the fungi or the materials, plants, the soil or seedsto be protected against fungal attack with an effective amount of acompound of the formula I according to claim
 1. 9. A 2-substitutedpyrimidine according to claim 2 in which the phenyl group substituted byL_(n) is the group B

where # is the point of attachment to the pyrimidine skeleton and L¹ isfluorine, chlorine, CH₃ or CF₃; L², L⁴ independently of one another arehydrogen, CH₃ or fluorine; L³ is hydrogen, fluorine, chlorine, cyano,CH₃, SCH₃, OCH₃, SO₂CH₃, NH—C(═O)CH₃, N(CH₃)—C(═O)CH₃ or COOCH₃ and L⁵is hydrogen, fluorine, chlorine or CH₃.
 10. A 2-substituted pyrimidineaccording to claim 3 in which the phenyl group substituted by L_(n) isthe group B

where # is the point of attachment to the pyrimidine skeleton and L¹ isfluorine, chlorine, CH₃ or CF₃; L², L⁴ independently of one another arehydrogen, CH₃ or fluorine; L³ is hydrogen, fluorine, chlorine, cyano,CH₃, SCH₃, OCH₃, SO₂CH₃, NH—C(═O)C₃, N(CH₃)—C(═O)CH₃ or COOCH₃ and L⁵ ishydrogen, fluorine, chlorine or CH₃.
 11. A 2-substituted pyrimidineaccording to claim 4 in which the phenyl group substituted by L_(n) isthe group B

where # is the point of attachment to the pyrimidine skeleton and L¹ isfluorine, chlorine, CH₃ or CF₃; L², L⁴ independently of one another arehydrogen, CH₃ or fluorine; L³ is hydrogen, fluorine, chlorine, cyano,CH₃, SCH₃, OCH₃, SO₂CH₃, NH—C(═O)CH₃, N(CH₃)—C(═O)CH₃ or COOCH₃ and L⁵is hydrogen, fluorine, chlorine or CH₃.
 12. A 2-substituted pyrimidineof the formula I

in which the index and the substituents are as defined below: n is aninteger from 1 to 5, where at least one substituent L is located in theortho-position on the phenyl ring; L is nitro, —C(═S)—N(A′)A, or—C(NA′)—SA, m is 0, 1 or 2; A, A′, A″ independently of one another wehydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkenyl, phenyl, where the organic radicals may be partiallyor fully halogenated or may be substituted by cyano or C₁-C₄-alkoxy; orA and A′ together with the atoms to which they are attached are a five-or six-membered saturated, partially unsaturated or aromatic heterocyclewhich contains one to four heteroatoms from the group consisting of O, Nand S; R¹ is C₃-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₃-C₁₀-alkynyl,C₃-C₁₂-cycloalkyl, C₃-C₁₀-cycloalkenyl or a five- to ten-memberedsaturated, partially unsaturated or aromatic heterocycle which isattached via carbon and contains one to four heteroatoms from the groupconsisting of O, N and S, R² is halogen, cyano, C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy orC₃-C₄-alkynyloxy, where the alkyl, alkenyl and alkynyl radicals of R²may be substituted by halogen, cyano, nitro, C₁-C₂-alkoxy orC₁-C₄-alkoxycarbonyl, where the aliphatic, alicyclic or aromatic groupsof the radical definitions of L, R¹ and/or R² for their part may bepartially or fully halogenated or may carry one to four groups R^(u):R^(u) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀alkynyl,C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═O)-A,—C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)—C (═O)-A,N(A″)—C(═O)—N(A′)A, S(═O)_(m)-A, S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A,where m, A, A′, A″ are as defined above and where the aliphatic,alicyclic or aromatic groups for their part may be partially or fullyhalogenated or may carry one to three groups R^(v), R^(v) having thesame meaning as R^(u); R³ is cyano, CO₂R^(a), C(═O)NR^(z)R^(b),C(═O)—N—OR^(b), C(═S)—NR^(a)R^(b), C(═NOR^(a))NR^(z)R^(b),C(═NR^(a))NR^(z)R^(b), C(═O)NR^(a)—NR^(z)R^(b),C(═N—NR^(z)R^(c))NR^(a)R^(b), C(═O)R^(a), C(═NOR^(b))R^(a),C(═N—NR^(z)R^(b))R^(a), CR^(a)R^(b)—OR^(z), CR^(a)R^(b)—NR^(z)R^(c),ON(═CR^(a)R^(b)), O—C(═O)R^(a), NR^(a)R^(b), NR^(a)(C(═O)R^(b)),NR^(a)(C(═O)OR^(b)), NR^(a)(C(═O)—NR^(z)R^(b)), NR^(a)(C(═NR^(c))R^(b)),NR^(a)(N═CR^(c)R^(b)), NR^(a)—NR^(z)R^(b), NR^(z)—OR^(a),NR^(a)(C(═NR^(c))—NR^(z)R^(b)), NR^(a)(C(═NOR^(c))R^(b)); where R^(a),R^(b), R^(c) independently of one another are hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl or C₄-C₆-cycloalkenyl;R^(b′) has the same meanings as R^(b), except for hydrogen; R^(z) hasthe same meanings as R^(a) and may additionally be —CO—R^(a); where thealiphatic or alicyclic groups of the radical definitions of R^(a),R^(b), R^(c) or R^(z) for their part may be partially or fullyhalogenated or may carry one to four groups R^(w): R^(w) is halogen,cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, and where two of the radicalsR^(a), R^(b), R^(c) or R^(z) together with the atoms to which they areattached may form a five- or six-membered saturated, partiallyunsaturated or aromatic heterocycle which contains one to fourheteroatoms from the group consisting of O, N and S.
 13. A compositionsuitable for controlling harmful fungi which comprises a solid or liquidcater and a compound of the formula I according to claim
 12. 14. Amethod for controlling phytopathogenic harmful fungi which comprisestreating the fungi or the materials, plants, the soil or seeds to beprotected against fungal attack with an effective amount of a compoundof the formula I according to claim
 12. 15. A 2-substituted pyrimidineof the formula I

in which the index and the substituents are as defined below: n is aninteger from 1 to 5, where at least one substituent L is located in theortho-position on the phenyl ring; L is halogen, cyano, cyanato (OCN),C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₆-alkoxy,C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═O)-A,—C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′)-C(═O)-A,N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A, S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A, m is0, 1 or 2; A, A′, A″ independently of one another are hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkenyl, phenyl, where the organic radicals may be partiallyor fully halogenated or may be substituted by cyano or C₁-C₄-alkoxy; orA and A′ together with the atoms to which they are attached are a five-or six-membered saturated, partially unsaturated or aromatic heterocyclewhich contains one to four heteroatoms from the group consisting of O, Nand S; R¹ is C₃-C₁₀-alkyl, C₃-C₁₀-alkenyl, C₃-C₁₀-alkynyl,C₃-C₁₂-cycloalkyl, C₃-C₁₀-cycloalkenyl or a five- to ten-memberedsaturated, partially unsaturated or aromatic heterocycle which isattached via carbon and contains one to four heteroatoms from the groupconsisting of O, N and S, R² is halogen, cyano, C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy orC₃-C₄-alkynyloxy, where the alkyl, alkenyl and alkynyl radicals of R²may be substituted by halogen, cyano, nitro, C₁-C₂-alkoxy orC₁-C₄-alkoxycarbonyl, where the aliphatic, alicyclic or aromatic groupsof the radical definitions of L, R¹ and/or R² for their part may bepartially or fully halogenated or may carry one to four groups R^(u):R^(u) is halogen, cyano, C₁-C₈-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkenyloxy, —C(═O)-A,—C(═O)—O-A, —C(═O)—N(A′)A, C(A′)(═N—OA), N(A′)A, N(A′) -C(═O)-A,N(A″)-C(═O)—N(A′)A, S(═O)_(m)-A, S(═O)_(m)—O-A or S(═O)_(m)—N(A′)A,where m, A, A′, A″ are as defined above and where the aliphatic,alicyclic or aromatic groups for their part may be partially or fullyhalogenated or may carry one to three groups R^(v), R^(v) having thesame meaning as R^(u); R³ is C(═S)—NR^(a)R^(b); where R^(a) and R^(b),independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl or C₄-C₆-cycloalkenyl; where thealiphatic or alicyclic groups of the radical definitions of R^(a) andR^(b)for their part may be partially or fully halogenated or may carryone to four groups R^(w); R^(w) is halogen, cyano, C₁-C₈-alkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy,C₂-C₁₀-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,C₃-C₆-cycloalkoxy, C₃-C₆cycloakenyloxy, and where two of the radicalsR^(a) and R^(b) together with the atoms to which they are attached mayform a five- or six-membered saturated, partially unsaturated oraromatic heterocycle which contains one to four heteroatoms from thegroup consisting of O, N and S.
 16. A composition suitable forcontrolling harmful fungi which comprises a solid or liquid carrier anda compound of the formula I according to claim
 15. 17. A method forcontrolling phytopathogenic harmful fungi which comprises treating thefungi or the materials, plants, the soil or seeds to be protectedagainst fungal attack with an effective amount of a compound of theformula I according to claim 15.